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Okolona native, and former NFL star Jack Gregory dies

Gregory was 74 years old.

Posted: Mar 2, 2019 8:36 PM
Updated: Mar 2, 2019 11:06 PM

MONROE COUNTY, Miss. (Obituary) - Jack Gregory, Jr., longtime legendary NFL player, farmer, businessman, philanthropist and Chief Executive Officer of the Mississippi Association of Supervisors, tackled the last obstacle of sickness and received the victory at 6 a.m. Saturday, March 2nd in Monroe County at age 74.

Known affectionately and respectfully by most as “Big Jack”, the 6’ 5’ giant of a man was born in Tupelo to the late Earl Jackson “Jack” Gregory, an NFL All Star in his own right, and Earlene McComb Gregory.

Gregory family

A man with a gregarious personality and vivacious wit, Gregory graduated from Okolona High School in l962 where he was an award winning standout and All-Conference athlete in football, track and basketball.

Gregory accepted a scholarship to play college football at the University of Tennessee, Chattanooga where he was an Honorable Mention All-American playing tight end for the Moccasins.  Although drafted his junior year, he instead transferred to Delta State University where he graduated and set the DSU college record with 557 yards as a tight end.

His pro football career began with the Cleveland Browns, the team his father played for in the l940s. A dominating defensive end, he excelled as a defensive end and tackle, becoming one of the most ferocious quarterback sackers in the NFL.  In l970, in the Browns opening game against the New York Jets, Gregory sacked legendary quarterback Joe Namath in the first televised Monday Night Football game.

Jack became the first free agent in Cleveland Browns history and chose the New York Giants. In l972, Gregory had his finest season, leading the NFL with 21 quarterback sacks, making him NFL Defensive Player of the Year runner-up.

Gregory retired from professional football in 1979, playing his last season with his beloved Browns.

Gregory returned to Mississippi and became a model civic activist, philanthropist, farmer and businessman. He loved the lands of Chickasaw and Monroe County where he farmed its lands and raised cattle.

He formerly owned Jack Gregory Enterprises, a furniture manufacturing firm.  Gregory devoted many hours to his favorite charity, the Easter Seals Campaign where he served several times as National Campaign Chairman and National Board President in l988, achieving the designation as longest serving professional athlete telethon chairman in the organization’s long history.

Gregory became a talent scout for the Denver Broncos.  He was a licensed professional auctioneer, and was founder, president and ringmaster for Rebel Auction Company.

In l993, he was chosen to be executive director of the Mississippi Association of Supervisors, a position he held for 11 years.  An Okolona and Northeast Mississippi icon, Gregory enjoyed his last years being a citizen and purveyor of good times and strong fellowship with his thousands of friends from everywhere.

A former Mississippi National Guard member, he was a lifelong member of the Okolona Presbyterian Church, the Okolona Country Club and the Okolona American Legion.

A service celebrating his life will be held at 1 p.m. Monday, March 4, 2019 at the Okolona Presbyterian Church with Rev. Dr. Randy Lewman and Rev. Jimmy Bryan officiating. Burial will be in the Gregory family plot at Oddfellows Cemetery. Visitation will be from 3 p.m. to 5 p.m. on Sunday, March 3 at Holland Funeral Directors-Okolona Chapel and from 11 a.m. to service time on Monday at Okolona Presbyterian Church.

Big Jack leaves behind his wife, Susan Brooks Gregory of Okolona, who he married Aug. 7, 2000; his son, E. J. Gregory, III and his wife, Charla of Oxford and a daughter, Madison Brook Gregory of Canton; two step children, Michael Carter (Brandy) of Wren and Amanda Hicklin (Eric). His grandchildren, Riley, Sydni, Thomas, Lucas and Ayden. His only brother, Judge John Andrew Gregory (Claire) of Okolona, and his family, and thousands of friends across Mississippi and around the country. He was preceded in death by his parents and first wife, Gwen Massey Gregory.

Memorials may be made to Okolona Presbyterian Church, 118 Robertson St., Okolona, MS. 38860, Tupelo Lee Humane Society, P. O. Box 2143, Tupelo, MS. 38801 or to Wags, 1317 Old Hwy 6, Amory, MS. 38821. Condolences may be e-mailed to

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